This module aims to give students a strong foundation in the fundamental principles of chemical reactivity, and introduces important physical-organic chemistry concepts. It builds on the student's knowledge of organic functional groups and how they react to form a variety of products using reaction pathways commonly used to make drugs and related compounds. The use of IR and NMR spectroscopy in monitoring organic reactions and characterising organic compounds will be introduced. The module also introduces the student to the conformational and 3-dimensional properties of organic compounds and how they can be analysed.
Review of functional groups and identification using spectroscopy
Functional group review; Introduction to IR and NMR spectroscopy and how they are used to monitor reactions and characterise organic compounds
Organic molecular bonding.
General concepts; Hybridisation (sp3, sp2 and sp); Drawing Lewis Structures
Organic acids and bases.
Organic acids and base classification (Brønsted-Lowry and Lewis); factors that affect acidity and basicity, including resonance, induction, steric and substituent effects; Dissociation constants and pKa (Henderson-Hasselbalch equation) – importance in physic-chemical drug properties and synthetic reactions (e.g. choice of acidic and basic reagents); theory and use of organic buffers; keto-enol tautomerism and enolates
Chirality and 3D properties
How to identify enantiomers and draw chiral compounds using the Cahn-Ingold-Prelog sequence rules – R,S terminology; polarimetry and measurement of optical activity
Conformations of alkanes & cycloalkanes.
Saw-horse and Newman projections; geometry of alkanes and potential energy diagrams – staggered and eclipsed conformations; geometry of cycloalkanes; conformations of cyclohexanes including chair and boat conformations – axial and equatorial positions; A1,3 strain; stability of cyclohexane conformations.
Structures/resonance – drawing resonance hybrids including with charges; Electrophilic Aromatic Substitution reactions - mechanisms; ortho, meta, para directing groups and effects of directing groups on reactivity; IR and NMR spectra of simple organic compounds – effects of substituents on appearance of spectra.
Chemical Reactions and Mechanisms
Nucleophiles (hard and soft) and electrophiles; Mechanisms of Substitution reactions (SN1 and SN2) and Elimination reactions (E1 and E2); Solvent effects on reaction mechanisms; Free Energy Diagrams; Addition reactions and mechanisms for functional groups, including alkene/alkyne additions (Markovnikov’s rule revisited); acetylation, esterification, amide coupling mechanisms
|Module Content & Assessment